Safety vs Efficiency in the Development of a High-Energy Compound

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 1043-1047

  Ruggeri, Sally Gut ^a   Bill, David R ^a   Bourassa, Dennis E ^a   Castaldi, Michael J ^a   Houck, Tim L ^a   Brown Ripin, David H ^a   Wei, Lulin ^a   Weston, Neil ^a,b  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 (2 CARBOXYPYRIDIN 2 YLOXY)BENZ[1,2,5]OXADIAZOLE; BENZOFURAN DERIVATIVE; NICOTINE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; DECOMPOSITION; ENERGY; REACTION ANALYSIS; SAFETY; SYNTHESIS; TEMPERATURE;

EID: 0347996080     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0341059     Document Type: Article

References (8)

1. Additional safety testing was carried out on this step, including accelerating rate calorimetry (ARC) and vent-sizing experiments. The data from these experiments indicated that adequate engineering controls were not possible in the intended manufacturing equipment.
2. For a general review, see Boulton, A. J.; Ghosh, P. B. Adv. Heterocycl. Chem. 1969, 10, 1.
3. Pollet, P.; Gelin, S. Synthesis 1979, 977.
4. Mallory, F. B. Organic Syntheses; John Wiley & Sons: New York, 1963; Collect. Vol. IV, p 74.
5. Some benzofuroxans have been defined as explosive. See: Gaughran, R. J.; Picard, J. P.; Kaufman, J. V. R. J. Am. Chem. Soc. 1954, 76, 2333.
6. Baldwin, J. J.; Claremon, D. A.; Elliott, J. M. Ponticello, G. S.; Remy, D. C.; Selnick, H. G. U.S. Patent 5,032,604, 1991.
7. In a pilot run, the reaction was run with granular potassium carbonate, and the reaction took 20 h instead of less than 4.
8. The overall system pressure was kept slightly below ambient pressure with partial vacuum pulled through the two in-line scrubbers containing an aqueous mixture of sodium hydroxide and sodium bisulfite to trap any chlorine formed.